Career
Under the tenure of Paolo Di Canio, he served as both Assistant Manager, and later Caretaker Manager following Di Canio"s resignation at Swindon Town. Following the announcement of Di Canio as Head Coach at Sunderland on 31 March 2013, it was confirmed Piccareta would reprise his role as Assistant Manager at the club a position he still holds. In 2001, Piccareta obtained his Union of European Football Associations B license and went on to coach with Italian lower league outfit Sanremese.
Piccareta left Biancoazzurri in 2005 to take up a position with Serie A giants Internazionale.
His role at Inter involved working within the Inter Campus Abroad project lieutenant was a job that took him all over the world coaching in China, Cambodia, Iran, Colombia, Cuba and Slovakia among others
Between 2008 and 2011 Piccareta focused his time coaching fellow coaches and acting as a first team coach at Italian lower league clubs. In May 2011, Piccareta was named assistant manager to Paolo Di Canio at English lower league club, Swindon Town.
Piccareta spoke of sharing footballing philosophies with Di Canio setting out a plan to bring a "strong identity" to Swindon along with an "Italian methodology in training" and that their "kind of football won"t be boring for the fans".
On 18 February 2013, Paolo Di Canio announced his resignation from Swindon Town, leaving Piccareta in caretaker charge. On 31 March 2013, after Paulo Di Canio was announced as the new Head Coach of Sunderland, it was confirmed that Piccareta would be following Di Canio to the Stadium of Light. On 31 May 2014 he obtained the Union of European Football Associations A licence from the Scottish FA course in Largs.
In November 2014 he started his Pro Licence course with the Scottish FA. On 7th February 2015 Piccareta join Portuguese Second Division club Olhanense in co-management with his fellow Italian Cristiano Bacci.
After 3 months the duo saved the Club from the relegation leading them to the 18th place. In July 2015 Piccareta signed a contract as academy coach of Sampdoria.